Synthetic method of 2-bromo-5-iodotoluene

A synthesis method and technology of iodotoluene, which is applied in the field of synthesis of 2-bromo-5-iodotoluene, can solve the problems of unsuitability for large-scale production and low efficiency, and achieve reliable oxidation performance, improved yield and quality, and less difficult control Effect

Inactive Publication Date: 2015-11-04
江苏威格瑞斯化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Phosphorus oxychloride is a highly toxic and dangerous product, microwave equipment requires special requirements, and the product is separated by column chromatography, which has low efficiency and is not suitable for large-scale production

Method used

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  • Synthetic method of 2-bromo-5-iodotoluene
  • Synthetic method of 2-bromo-5-iodotoluene
  • Synthetic method of 2-bromo-5-iodotoluene

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Experimental program
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Effect test

Embodiment 1

[0046] Step 1 Iodo

[0047]Put 82mL of ethyl acetate and 101mL of glacial acetic acid into a 500mL four-neck flask, then put in 20.43g of iodine powder, 13.57g of sodium percarbonate, and 18.41g of o-toluidine. There is an exotherm from acid-base neutralization, and stir under normal water cooling conditions. , to obtain a dark brown clear solution with a small amount of small solid particles of sodium acetate suspended. Use a constant temperature water bath to keep the reaction temperature at 27°C±1°C for 1 hour and 30 minutes, then heat the water bath to 53°C to raise the temperature of the reaction solution to 48°C, and continue to keep warm for 2 hours and 32 minutes. After 2 hours and 32 minutes, the color of the reaction solution has changed significantly. shallow. Take the reaction liquid onto the filter paper and observe for 5 minutes. The brown spots are stable in color and there is no fading caused by iodine sublimation, indicating that the reaction of iodine is bas...

Embodiment 2

[0051] Step 1 Iodo

[0052] Put 323mL of ethyl acetate and 406mL of glacial acetic acid into a 2000mL four-neck flask, then put in 81.23g of iodine powder, 53.84g of sodium percarbonate, and 73.21g of o-toluidine, and stir under normal water cooling conditions to obtain a dark brown clear solution, suspend A small amount of sodium acetate solid small particles. Use a constant temperature water bath to keep the reaction temperature at 29°C±1°C for about 1 hour and 30 minutes, then heat the water bath to 54°C, and the temperature of the reaction solution rises to 49°C, and continue to keep warm for about 3 hours. Add 6.23g of sodium sulfite, stir for 30 minutes and then filter off the insoluble salt. Heat the filtrate with a water bath, distill off the mixed solvent under normal pressure, and then switch to vacuum distillation at -0.075Mpa. After about 40 minutes, almost no solvent is evaporated, and finally vacuum -0.085Mpa, water bath 96.7°C, bottle The internal gas phase te...

Embodiment 3

[0056] Step 1 Iodo

[0057] 407 mL of ethyl acetate and 502 mL of glacial acetic acid were put into a 2000 mL four-neck flask, and then 101.84 g of iodine powder, 67.08 g of sodium percarbonate, and 91.44 g of o-toluidine were added. Use a constant temperature water bath to keep the reaction temperature at 29°C±1°C for about 1 hour and 30 minutes, then heat the water bath to 54°C, and the temperature of the reaction solution to 48°C, and continue to keep warm for about 3 hours. Add 7.36g of sodium sulfite, stir for 30 minutes and filter off insoluble salts. Under heating in a water bath, evaporate the mixed solvent from the filtrate under normal pressure, and then switch to vacuum distillation at -0.075Mpa. After about 40 minutes, almost no solvent is evaporated, and finally vacuum -0.085Mpa, water bath 96.4°C, in the bottle The gas phase temperature is about 87°C, and the tan viscous liquid remaining in the bottle is 4-iodo-2-methylaniline.

[0058] Step 2 diazotization of ...

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Abstract

The invention discloses a synthetic method of 2-bromo-5-iodotoluene. The product is prepared by using o-toluidine as a staring material through iodination, diazotization and bromination, wherein in the step of iodination, iodine powder is used as an iodination reagent, sodium percarbonate is used as an oxidizing agent and an ethyl acetate / glacial acetic acid mixed solution is used as a solvent; the steps of diazotization and bromination are completed by adopting a one-pot method, and sodium nitrite and hydrobromic acid are used as reaction reagents and copper powder / copper bromide is used as a bromination catalyst in the steps. The method for synthesizing 2-bromo-5-iodotoluene by utilizing the process route has the advantages that the raw materials in the step of iodination are safe and accessible; the process is simple and convenient to operate; the reaction conditions are mild; the raw material conversion rate is high; the total mole yield of iodine atoms can be 72% or above; the steps of diazotization and bromination are combined, are completed by the one-pot method and are simple and convenient to operate; few byproducts are generated; hydrobromic acid can be used indiscriminately multiple times after being treated, so that the cost is saved and the material is more environment-friendly.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a synthesis method of aromatic ring halogenated aromatic hydrocarbons, in particular to a synthesis method of 2-bromo-5-iodotoluene. Background technique [0002] 2-Bromo-5-iodotoluene is an important synthetic raw material for the treatment of depression, diabetes, hypertension, rheumatism and other diseases, and it is widely used. [0003] The literature (Applied Chemistry, 2012, 41(7): 1291-1293) reported an improved synthesis process of 2-bromo-5-iodotoluene, using o-toluidine as a raw material, and preparing it through the iodo and diazotized bromo routes product. In the method reported in this document, sodium periodate is used as an oxidizing agent in the iodation step, and iodination is carried out in a mixed system of acetic anhydride, glacial acetic acid, and concentrated sulfuric acid, and the intermediate must be used after recrystallization and purification. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/093C07C25/02C07C209/74C07C211/52
Inventor 邓季明
Owner 江苏威格瑞斯化工有限公司
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